


Roll for Initiative

by themoonandotherslikeit



Category: Supernatural
Genre: Destiel - Freeform, Dungeons and Dragons, Fluffy, Funny, Humor, Language, M/M, Sass, dnd, nerdy
Language: English
Status: Completed
Published: 2019-04-19
Updated: 2019-04-19
Packaged: 2020-01-16 05:56:21
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,344
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18515284
Author URL: https://archiveofourown.org/users/themoonandotherslikeit/pseuds/themoonandotherslikeit
Summary: After a little convincing, Charlie starts up a new tradition in the Men of Letters Bunker. Thursday night Dungeons and Dragons. After playing for an hour, the boys come across a foe that is a little more challenging. Can friendship and sass get them through the carefully made story that Charlie has created, or will they spend ten sessions arguing about if Castiel’s character dumb, or actually pretty creative?





	Roll for Initiative

__

_The sun was low in the sky as the Winchester brothers climb up the hill. Castiel follows behind, keeping up on Deans heels. Injured in a previous battle, Dean holds tightly to his quarterstaff, leaning on it a little more than he should. Sam takes out his map of the area. They hope that once they were over the large hill that they would be able to see their surroundings more clearly. Instead, when they reached the top of the hill they stood face to face with a large, hulking Great Orc. It stared down at the party with large bottom teeth, dripping with thick saliva._  
  
“That’s so fucking gross.” Dean cackled, as he took a swig of his beer.  
  
“Let me finish.” Charlie hissed, shooting an expression to her friend that sat next to her at the kitchen table in the bunker. “Like I was saying…”  
  
_The Orc pulled his ax above his head with a scream that was almost unholy. It rages through your bones, like nails on a chalkboard._  
  
“What do you do?” She asked eagerly, her palms flat on the table.

“I’m gonna hit it with my staff.” Dean said.  
  
“Make an attack roll.”  
  
Dean fluttered his eyelashes, adjusted the hood of his black cloak, and dramatically shook his twenty sided dice before letting it go on the table. The group held its breath, to see if Dean could take out the Orc’s kneecap so they could escape.  
  
“Aw fuck.” He said, letting his upper body flop on the table in defeat. “Nat one.” 

  
“You try to bring up your quarterstaff, not considering the fact that you still have an injured leg, and you literally collapse at the Great Orc’s feet. If he were in a laughing mood he would laugh at you, but he isn’t, because he’s an Orc.” Charlie shrugged.  
  
“Why is it that I can kill monsters so easily in real life, but in game this fucking piece of plastic can determine my skills?” He picked up the dice, eyeing it with annoyance.  
  
“You shouldn’t have put all of your stats in Charisma, Dean.” Sam said, as if it were obvious.  
  
Dean turned and glared at his brother. “I was hoping to pick up some hot elf chicks. You’ve gotta have charisma to pick up chicks, Sammy. Not that you’d know.”  
  
“I do not understand this game.” Cas huffed.  
  
“Okay, nerds. What are you going to do? Focus.” Charlie said, leaning into the table. She was eager to move on with the encounter.  
  
“What do I know about Orc’s?” Sam asked, cheerfully.  
  
“Do a history check.”  
  
Sam rolled the dice gently onto the table before sighing. “Five.”  
  
“You know plenty about regular Orc’s but this is a Great Orc, Sam. It’s fucking great. You don’t know squat.” Charlie’s eyes flickered to Castiel. She smiled widely. “What about you, Cas?”  
  
Castiel met Charlie’s eyes seriously. “I would like to smite it with my angelic grace.”  
  
The group turned their attention to Cas. “Uh, that’s nice, Cas, but your character is a cat so you don’t exactly have that ability.”  
  
Cas frowned, looking down, his cat ears slipping a bit at the angle of his head. “I would like to see the rules again.” He complained.  
  
“Why did you make your character a cat, Cas? It doesn’t even have any magical abilities.” Sam asked with genuine curiosity.

  
Cas sat up a little straighter, prepared to argue his case. “Felines have many useful abilities, Sam.”  
  
“They just make me sneeze.” Dean complained.  
  
“That is useful ability number one! If your enemy is sneezing they are incapacitated and there for, unable to see for a moment. It is the perfect time to strike.”  
  
Charlie raised an eyebrow.  
  
Cas cleared his throat. “I would like to induce an allergy attack.”  
  
“Uh… roll for attack.”  
  
Castiel gave the guys a deadpan expression as he shook his dice in his fist before letting it go.  
  
“You’ve got to be fucking kidding me!” Dean groaned.  
  
“That would be a natural twenty.” Cas said flippantly.  
  
“Christ.”  
  
“Cas rubs up against his leg and he falls into a sneezing fit. His body racked with sneezes.” She eyed Dean. “And since you’re so close to him when he pulls his head back for a huge sneeze, a elastic, wet, green droplet of snot drips down and lands right between your eyes.”

“God this thing is so fucking gross!” Dean complained.

“What are you doing now?” Charlie asked.

  
“We should run.” Sam nodded.  
  
“Easy for you to say! My leg is busted up.” Dean complained, wiping the fake snot off his face.  
  
“I can run very fast as a cat.” Castiel said with a grin. “Perhaps _you_ picked the wrong race.”  
  
“I think we hurt his feelings.” Sam said, eyeing Cas.  
  
“Make a decision, boys!” Charlie urged them on, trying to keep the pace.  
  
“Fine, let’s run.” Dean grumbled.

“Make a dex roll, Dean.” Charlie’s eyes narrowed at him.

Dean whispered profanities under his breath and tossed his dice. It rolled and bounced and fell to the ground. Dean leaped out of his chair and got on his hands and knees to view the number. By some grace of God he rolled a nineteen. “Fuck yes! Finally!”

“You manage to hobble away.” Charlie put her hands together.

  
“Alright, I say we head to the city to see if we can get Dean some medical attention.” Sam turned to his brother and adds, “so try not to die before we get there.”

“Just use a spell to heal me, Sammy. Come on, you have the spell slots.”

“Yeah, no way in Hell, man.” Sam said, dismissively. “I’m not wasting my spell slots to heal you. Being in a group with you means we will definitely be in a fight again soon. We are going to need those spell slots.”

“We’re definitely going to need those spell slots.” Dean mumbled in annoyance.

“Let’s go.” Sam said turning to Charlie. “Okay, we will head to the city.”

Charlie nodded and flipped through a few papers behind her block. She eyed the three men in front of her with a quirked eyebrow. She pushed a red curl out of her eye and smirked. Dean had a feeling this wasn’t going to end well.

_“Dungeons and dragons? You’ve got to be kidding me?” Dean turned to Charlie, with his arms crossed._

_“I’m not.” Charlie said, offended. “It’s fun, Dean. You seriously never played as a kid?”_

_“I didn’t exactly have a normal childhood.” He laughed. “Who would I have played with? Sammy?”_

_She shrugged. “I’m not going to say I had a million friends growing up either. Nerds always find a way.”_

_“Fine, I’ll bite. What’s the deal with the dungeons game? Just a bunch of geeks sitting around, not having sex, yeah?”_

_Charlie snorted and rolled her eyes. “Come on, Dean, you’re not that simple. Open up your big gorilla brain, and I think you’ll like what you hear. Imagine this… you’re in a magical land. Lush, green, beautiful. You’re a hero, or a villain, depending on your schtick. You and a group of companions are on a quest, fighting monsters along the way. No one gets hurt, not really, and everything is based on luck and skill. It’s a chess board that you can manipulate. In a world that I create for you. There are swords, and magic. Elves, wizards, dragons…”_

_Dean raised an eyebrow. He could almost picture it. He’d done nerdy things with Charlie before, they frequently went to Renaissance festivals together, and if he was honest this didn’t seem that different. “So, what, I’m a wizard Charlie?”_

_Charlie shrugged and tossed a book to Dean. “Or something cooler.” She raised an eyebrow. “But I always appreciate a good Harry Potter reference.”_

“You’ve made your way to the city after half a day of walking. Dean you’re really fucking tired, and your leg is aching, at best. The city is a port town, by the shore. All the typical buildings are involved. There’s a blacksmith, a tavern, a few places of worship.”

“Anywhere to get some healing?”

Charlie shrugged and Dean groaned in response. “I guess I’ll go to the tavern and see what I can drum up.”

“I’d also like to go to the tavern to procure a place to sleep tonight.” Sam nodded.

The three looked to Cas, who had been surprisingly quiet since the Orc attack. “I would like to find a home to take me in, since my companions don’t appreciate me.”

“Cas, come on.” Dean groaned. “Just come to the tavern with us.”

“No.”

“What? You want some catnip or something? Don’t be so difficult.”

“I’m not going, Dean.”

“I want to make him come.” He said to Charlie. “He’s a cat, surely I can convince him.”

Charlie shrugged. “Roll an animal handling.”

Dean nodded, feeling like his luck was getting better. He took his dice in his hands and rolled them in his fingers. His eyes never left Castiel’s. They were challenging the angel.

He let the dice go. It rolled onto the table, but Dean’s eyes never left Cas’. “I own you, cat.”

“No, you don’t.” Sam snorted. “You rolled a three.”

“Yeah, you can’t seriously think that you can bag a cat, Dean. It’s not that easy.” Charlie said with a laugh. “Cas, obviously it doesn’t work.”

“I purr.” Cas grinned at Dean and gave him a wink.

“Christ.” Dean rubbed his face. “Can we call a truce?”

“A truce?” Cas raised an eyebrow. “Pray tell, why should I do that?”

“Because we are supposed to be a team, man. Me, you, and Sammy.”

Cas tapped his chin and looked at Sam. “I have no problem with Sam.”

“Of course you don’t.”

The angel shrugged. “Maybe I just expect less from him.”

“Rude!” Sam groaned. “I’d like to attempt to pet Cas, to show him that I care.”

“Cas? Are you going to let him pet you?” Charlie asked, eyeing the angel.

Cas narrowed his eyes, like he was really thinking it through. “I will allow it.”

“I’m going to scratch under your chin.”

“I will allow you to carry me, if you wish.”

“Sure, man. I’ll carry you. Want to go to the tavern?”

“If I can get fish there, I will allow you to take me there.”

“The fuck?” Dean complained.

“Sam has a way with felines that you don’t, Dean.” Castiel said flippantly.

“Of fucking course he does.”

“Are you jealous?” Charlie asked, her eyes flickering to Dean.

“Jealous of Sammy? Please. I want to go to the tavern to pick up elf chicks.” He crossed his arms.

Charlie nodded. “After looking around for a bit you locate a tavern.”

“I want a beer.”

“Two silver pieces.” Charlie spouts, in a ridiculous old world accent.

Dean sorts in response and nods. “Yeah, okay. I want to scope for Elf chicks.”

“Roll an investigation.”

“That’s a fifteen.” Dean said proudly, when his dice landed on the table.

“There are a pair of female elves in the corner of the bar.”

“Hell yeah, I’m approaching.”

“Great, pause on that.” Charlie said, turning her attention back to Sam and Castiel. “Alright boys, what’s going on in your neck of the woods?”

“I would like to locate sustenance.” Castiel said simply.

“I want to research local lore, to see if there’s anything with this town.”

“Sam you’re supposed to be playing a character, not just yourself.” Dean complained.

“Yeah, coming from you. You’re in a bar trying to pick up chicks. Where’s the role play there?”

“You make a valid point.” Dean said quietly.

“Sam, can you take me to the tavern for the fish you promised?” Castiel questioned.

“Sure, buddy.” Sam turned to Charlie. “We go into the tavern. I’ll put Cas down so he can check the place out.”

“I’d like to go to the bar to try to purr, and meow until I get food.”

“I’ll allow it.” Charlie shrugged.

“I jump up on the bar and meow at the bartender.”

“Roll a persuasion.”

“That’s an eighteen.”

“Without asking what you need, he hands you a fish that he’d been cooking for another table.” Charlie said with a grin.

“I will eat it.”

“Dean back to you.”

“I want to flirt with the elves.”

Charlie laughed. “Yeah, okay. There are two female elves in the corner. What exactly are you doing to flirt?”

“I want to tell a story about the orc fight, where I was a real badass.”

Charlie narrowed her eyes. “So you want to lie to these poor girls to get them into bed?”

“Basically.”

“Roll performance, with disadvantage.”

“Disadvantage?” Dean complained.

“For being a pig.”

“Fair enough.” Dean rolled his dice twice, and took the lower of the two rolls, which just so happened to be a twenty-two with modifiers.

“You lucky bastard.” Charlie sighed. “The women love your story. They comment on how strong you are and how brave. They’re basically swooning.” She looked almost ill as she described it.

“Excellent.” Dean grinned and cleared his throat. “Ladies, may I escort you both to my room?”

“Oh, roll two persuasions. One for each girl.”

Dean rolled his eyes and rolled. He managed another twenty and a nineteen. “Ladies, let’s go upstairs. I’ll take real good care of you.” He wiggled his eyebrows.

“You are going to let him get away with this, Charlie?”

“It does seem a little unfeminist.” Sam agreed.

“I’m at the mercy of his rolls.” She said, defeated.

“I would like to go to Dean and the females.” Cas said, suddenly.

“Go ahead, Cas. Do your thing.”

“I am going to go up to Deans room and scratch on the door.”

Charlie rolls a dice behind her block. “One of the girls is afraid of the scratching and asks Dean to check it out.”

Dean groaned. “Fine. I’ll check on the door. I open it.”

“I walk right in.”

“Seriously?”

“I’m going to jump on the bed and hiss and swipe at the girls.”

Charlie rolled twice. “They’re screaming.”

“I want to really growl and scare them.” Cas said insistently.

“Ladies! Relax! I’ll get him out of here!” Dean said eagerly, with his hands up in defense.

“Dean is this your pet?” Charlie said in a valley girl voice, twisting her fingers in her curls.

“No, he is most certainly not my pet.”

“Oh my god! So you just let a stray feral cat in here?!” Charlie exclaimed.

“No… that isn’t what I said!”

“I am hissing and actively approaching the girls.” Castiel said with a mischievous grin.

“Roll intimidation!” Charlie said.

Castiel dramatically rolled the dice and let it hit the table. Nat twenty. Sam cheered, rising to his feet. “Fuck yes! Cas what is your luck, dude?”

“The two girls run screaming out of the room.” Charlie said with a grin.

Dean clenched his fists on the table and turned to the angel. “What the fuck, dude?”

“I want to curl up on Deans pillow and go to sleep.”

“The fuck you are.” Dean growled in annoyance. “I’m throwing both pillows on the floor. Now focus on my face. What. The. Flying. Fuck. Was. That. About?!”

Castiel shrugs and takes a drink from his beer, avoiding Dean’s eyes.

“No, no, no. We aren’t doing that shit. You’re really so mad that I insulted your character that you’re going to cock block me?”

“I am saving those women.” Cas said dramatically, with his hand on his chest.

“Saving them from what?”

“Disappointment?” Sam snarked, swallowing a laugh.

“I’m not talking to you.” Dean snapped with annoyance. He turned back to the angel. “Seriously.”

Castiel rolled his eyes and pinched the bridge of his nose. “Dean, we are on a quest! We have enemies to fight, and you’re worried about bedding women! Your priorities are not right.” Castiel mirrored Dean by crossing his own arms.

“You didn’t seem too concerned with the quest when you were snuggling up to Sam!” Dean stood up, and poked Castiel’s chest.

The angel rose to his feet almost immediately. “Not like you would ever hold me, Dean!”

“You’re a cat, Cas! I’m allergic!”

“You’re not allergic in game!”

The two were standing an inch from each other now. Breathing heavily. Their chests rose and fell. Charlie and Sam sat in intense suspense, watching the two. Charlie gripped her block in front of her, almost hiding, while Sam sat with his mouth hanging loose. Neither Cas or Dean noticed, though, they were in a world of their own. In Deans bedroom, in a Tavern, in a world that Charlie made up.

“Sorry that I want to be authentic!” Dean groaned, putting up his hood from his cape.

“Stop hiding from me, you coward!” Cas said, pushing the hood back down. He grabbed Deans face roughly in his hands, causing Deans green eyes to widen in surprise. Cas wasn’t rough with him. He was known to the the gentle one in the bunker.

“I’m not hiding, Cas.”

“Of course you are.” Castiel’s voice was low as his eyes landed on Dean’s lips, then flickered up to his eyes. “You always have been.”

Dean opened his mouth to argue with the accusation, but he couldn’t bring the words to his lips. He couldn’t say anything real with Cas that close. “God, get rid of these fucking things.” Dean grabbed the fabric cat ears off Castiel’s head and tossed them away. “You idiot.” Dean exhaled, putting a hand on each of Cas’ arms. “You fucking dumbass.”

“Yeah just keep insulting me.” Cas challenged. “It’s safer that way, right?”

“Why don’t you want me hooking up?”

“I don’t like you taking women home after hunts.”

“Why?”

“Because.” Cas hissed. “I want you to be with me after hunts.”

Dean frowned, looking confused. “But I am with you after hunts.”

“Not… not like that.”

It was like a light went off in Deans mind. _Of course_. It was all so clear, but Cas couldn’t possibly mean what it sounded like. Right? He didn’t want him to have sex with women because he… Christ.

“I don’t understand… So you…” Dean began, but before he could finish Castiel crashed into him. His lips pressed to Deans urgently, perhaps just to get him to shut the fuck up.

If that was his intention, boy did it work.

Dean melted against him, pulling Castiel close to him, chest to chest. Cas’ thumbs ran across Deans cheekbone, and he could feel Dean smile against his lips. He pulled away a bit and pressed his forehead to Deans. “Do you understand now?”

Dean was flushed, his cheeks pink. “I don’t know. Think you can explain it again?” A grin grew on his lips, exposing a perfect row of teeth. It was a challenge, one Cas was perfectly willing to meet.

“Fucking _finally_!” Sam cheered, his fist pumping in the air.

“I uh… think this is a great place to end the session.” Charlie said from behind her block, peeking at the two boys. She felt she was intruding, but she couldn’t hide her huge grin. “Sam, we should… uh… discuss some lore, somewhere else.”

“What?” Sam glanced at Charlie, and then at the two men that were still wrapped in an embrace. “Right, uh, lore… books. Sure. We will be back later.”

Cas and Dean stared at each other. “So if this is always going to happen during this game, I think we may have to let Charlie move in, because I’m going to have to play every day.” Dean said softly.

“Does that mean you’ll hold me, Dean?” Cas asked with a smirk. “Even if I’m a cat?”

“Buddy, I’ll hold you no matter what you are.”

Dean kissed him then. He kissed him like they’d do it a thousand times again, like he was made to kiss Castiel. Perhaps it was under the disguise of the game that cracked Dean open like an egg, or perhaps it was Cas’ jealousy for fictional characters, but it was the start of something. It was the start of everything.

**Author's Note:**

> This was a collaboration with the amazing Ella, who did the art piece for this fic! Follow her on tumblr @thescreechowl she is amazing!)
> 
> Yell at me at @themoonamdotherslikeit on tumblr :)


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